Reclaiming your retirement through WFH: Can you work for longer if you still love it?

A new, COVID-induced wave of home workers has swept the world. Among them are midlifers coming up to retirement. But working from home (WFH) has opened up a world of opportunity for budding entrepreneurs and potential retirees who want to keep their minds busy instead of putting their feet up.

WFH has provided flexibility and breathing space for many employees at a difficult time. While some businesses are expecting a return to the office environment, others are talking about making WFH an option moving forward as part of a flexible arrangement.

So many people find a common comfort in the WFH life. It has provided a new corporate culture that seems to value work/life balance, takes hours of sweaty commuting out of the day, and provides security while affording more time with your loved ones.

Which begs the question: If you’re more relaxed about work, why stop providing that security for yourself? Retirement could be decades away if work is no longer eating your energy and personal bandwidth as it once did.

Combining the self-discipline and relative comfort that accompany WFH with an entrepreneurial spirit can help you capture the best of both worlds. This is a golden opportunity to take hold of your ambitions and passions while keeping your mind busy during retirement.

WFH means that you make a substantial time and money saving in commuting costs. And what does any good entrepreneur do? They invest savings into their passions and visions, or they find opportunities to make money.

Even if you don’t have a hobby that easily allows for monetization, you can set up a business to maintain your income and stop retirement becoming a mind-vacant time in your life.

You feel great. You feel focused. You feel driven. And you love making money from home. So why retire? Team Vippi looks at ways to capture that entrepreneurial spirit and enter the next stage of your life on your own terms. 

Do you have unfulfilled ambitions or places you’ve really wanted to go? 

Some people see retirement as the land of opportunity for dropping their professional obligations and doing something they’ve always wanted to do. But why do you have to stop working to fulfil your ambitions?

Through their sacrifices over the years, people sometimes create a barrier between supporting their family financially and doing the one thing they really love. But your time WFHing has shown that you can stay disciplined and productive. You may have enough savings built up to finally take your passion and turn it into a business – and you may be able to source investors if you don’t have the funds yourself. 

You’ll very quickly find that you can source more energy if you:

  1. Do something you love that pays you rather than just doing something that pays you.
  2. Do something for you rather than someone else.
  3. Do something easy and self-generating that makes you money while you do fun stuff.

Retirement doesn’t need to be a surrender. Make it a reclamation. You can turn your home into your Personal and Professional Fulfilment HQ. 

Losing financial security might stress you out more than retiring

If you retire, there’s always the risk that you will outlive your savings with absolutely no way to claw it back once it’s gone.

Working means you stay financially nimble and secure. According to the American Psychological Association, financial and economic concerns are the top self-reported causes of stress. You might seem fine now, but if there’s an economic crash or extreme personal circumstance to account for and you have no more income, you’re not protected.

Are you really putting your feet up if your dwindling savings constantly play on your mind? WFHing for your own business and on your own terms means that you still have an income but can now live a flexible life.

But what if I want to travel?

Then do it. Put a hold message on your website or outsource the work temporarily and embrace the world. Maybe even take the work with you if your type of trade permits. You’ve proved you can work from home, but why not work from Thailand? India? Portugal? All you need is a laptop, or even just your phone, and a WiFi connection.

That’s the joy of being your own boss. Being your own boss in your own house? Even better. Being a boss on a beach in Fiji? Sign us up.

Traveling might also be a route to more business, better contractors, and new social connections. Let one part of your life feed the other.

What are the benefits and risks of retirement?

You might still be weighing up whether to keep working or dive into the unknown with retirement.

In short, the benefits of retiring include:

  • More time with your family
  • Time to relax 
  • The freedom to choose your next steps free of expectation
  • Less stress and pressure than employed life

The risks are serious and pretty much irreversible, including:

  • Outliving your funds
  • Increasing medical and memorial costs
  • Boredom
  • Grief (you will lose people)
  • Loneliness

If you decide to WFH during your retirement, the grief and loss will still suck. But you’re less likely to outlive your pension savings and still get to control elements of your life like seeing your family more, avoiding obligations to bosses, and reducing stress.

Squaring the social circle: Staying social with a WFH business 

Many people center their whole social world around their workplace. Is that a healthy approach? Not always, but you find good friends where you can.

Even when you WFH for an employer, though, there’s still the option of work holiday parties, socials, and the general office atmosphere (once businesses return to the office, of course). But running your own business? You can be the one throwing the damn parties. 

You’ve the opportunity not just to have a social circle, but also to become a fantastic social connector and a pillar of your community.

You can also run the business with friends. Say you’ve been a musician all your life and want to start a wedding band with some long-time collaborators who’ve also been tied to day jobs – now’s your chance! And you’re still being social.

Take control of obligations. 

When you’re WFH for an employer, people still expect things from you, and you might actually be compelled to do more work, just to prove that you are still doing what you’re supposed to.

No one’s saying running a business is easy. But you can have far more control over the forces vying for your mental space, from emails and WhatsApp messages pinging left, right, and centre to the expectation that you’ll work beyond your contracted hours.

When you run your own business from the comfort of your garage or home office, if you want to turn in early for the day, you can. If you want to keep plugging away because it’s a passion project, then you can do that too.

Many people retire to claim control back from people who expect far too much from them – but who’s to say you can’t do that by continuing to earn money your way?

How to set up a new business going into retirement

Business has now been democratized. The barriers for entry are far lower, and virtually anyone can set up a business with a good idea and the right mindset.

Base it on your passion or vision.

What didn’t your job give you that you want from an income?

Whether you’re an artist, want more of a chance to travel, or have a service like DIY that you can provide around your area, this is your opportunity to do what you love on your terms.

You might even simply have a good idea you want to try that doesn’t revolve around a hobby. Well, you finally have the time to put together a convincing business plan and approach investors.

Online business

Start a new craft business on Etsy. 

This is for craftier folks. But Etsy is an option if you love making stuff and want to convert that stuff into money

Anything from garden furniture to boutique sweets to ridiculous clothing is available on Etsy. Nothing seems to be off-limits as long as it’s fun, creative, and independent. People flock there for birthdays and seasonal gifts.

Etsy takes a listing fee for each item you put on the site, whether the item sells or not. But if you’ve enough belief in your craft and want to monetize it instead of retiring, it’s a fantastic option.

Sell items on Shopify or through local and national dealers.

It’s almost too easy to set up a seller account with a major online retailer. There’s usually a fee for different levels of subscription which you can increase as your business grows.

But if you want to sell antiques, historical items, or old records, for example, you’re certainly no longer restricted to flea markets.

Create an online profile and personal brand.

Use social media and build publicity for your service. Don’t just post statuses every now and again – what are you really about? Draw people into the story of your product through videos, tutorials, and starting a community.

Show your audience that you live and breathe your business, and that audience will grow.


A good idea has legs, and the recent wave of successful crowdfunded ventures shows that people are willing to put their money where their mouths are. In the U.S. alone, over $738 billion was crowdfunded in 2016 alone

That’s $738 billion people spent on dreams and products that don’t exist yet – and yours could be one of the businesses that benefits in the future. Have a look at GoFundMe and similar sites, and think about how you’d pitch your services to an unsuspecting public.

You’ll likely need to make a video and offer perks to potential crowdfunding investors, including one of your products. Crowdfunding is essentially a huge wave of presales you can use to build your business.

Apply for an SBA loan.

The US Small Business Administration helps to connect small businesses with loans.

They usually offer competitive rates and business support, and require lower down payments than direct private loans. Plus, they have lower overhead requirements and don’t even request collateral for some loans.

Requirements generally include the following:

  • You must run a legal, registered for-profit business.
  • You have to do business in the U.S. and be located there.
  • You need to have invested your own time and money into the business.
  • You must have exhausted all other options for lending.

There are several different types of SBA loans, and you don’t necessarily need an amazing credit score to get your application approved. You can find out more here.

Learn some other skills.

Own your niche, sharpen your skills, and take your passion to market.

For example, if you’re a great baker, learn how to write a little and use a camera so you can start a food blog. 

Find an angel investor.

These are private individuals who fund business ventures in exchange for an equity stake in the company.

While they may have a say in how the business is run and ask for a high rate of return (usually 25-60%), angel investors can be a great way to secure financing for a non-established business. What’s more, you don’t even have a legal obligation to pay them back if the business fails. 

Potential angel investors might include:

  • Family and friends (although if the business goes south, it could take the relationship with it)
  • Wealthy benefactors (some folks with money might be looking to multiply their savings in clever ways – your business might be one of those avenues)
  • Angel syndicates (private investors club together and fund investments through a syndicate management team)

You’ll need a business plan – and a very good one – if you want to go the route of angel investor financing. (You should have one anyway. Don’t go into any serious project blind.)

Collaborating with friends.

If you’re in a peer group with like-minded people at a similar stage of life, why not pool some resources and start a venture together? 

You can spread the risk between you and can pursue your passions while keeping your social life ticking over. You needn’t be good at the same thing – in fact, it helps to have varied skills within the team.

If your friend is a numbers whiz, but you’re the creative soul of the project, it removes from your plate the part of the business you might not want to deal with.

Obviously, the friendship is part of the equity on the line, and if it goes sour, it can cost you more than the invested cash. But a partnership or collaboration can be just the thing to add color to your reclaimed retirement.

Business incubators

These are programs that help you… well, incubate your business, really. They provide mentoring, investor access, and workspaces for young startups.

They might be run by a university, a non-profit organization, or a venture capital firm looking to ferment some tasty investment opportunities.

You would generally have to apply, interview, and receive a decision. Think of it as a university course, but the course is Your Business, and the diploma is A Bunch Of Money To Run Your Business.

Things to be aware of

Life comes at you fast. These are the aspects you should consider if you want to take control of your WFH life. You’re a multi-faceted, capable person who has juggled hundreds of responsibilities for your entire  life – but you only have so many resources.

Retirement might still be a viable option for you if:

  • You’re a caregiver. If you’re looking after a sick partner or family member on a near full-time basis, you might struggle to balance it with work obligations.
  • You have your own health problems. If you’ve started to develop severe physical or mental impairments, it might be time to take it easy on your mind and body.
  • You want a charity project you won’t earn money from. You’ll still be working, just not for money. You’ll have to think about ways to alleviate the economic stress. What is your pension portfolio like? Have you made stable investments in a stock portfolio to make your own money while you help others? You also have to look after yourself.
  • You have the savings and it’s what you really want. You may truly desire a quiet life on the ranch, making meals for the family and enjoying your time with your grandchildren. You could have other ways to occupy your mind while finding joy. If this applies, by all means retire. Just plan in advance and make sure it’s the right thing for you. And if you fixed up a whole ranch, you might be able to make a penny or two providing your talents around town.

Retirement isn’t for everyone – but neither is a life of work. Look at what’s truly important to you, and hone in on it.


WFH culture has opened up new doors for future retirees to reclaim their time in ways that steer away from tradition and provide financial security and fulfilment.

Retirement is a generally vacant time for people’s minds, and can be filled with grief, loneliness, and boredom. Of course, it can also be relaxing and freeing. But by building a WFH scenario to take you through retirement, you can occupy your mind during the darker moments, relieve some of the financial pressures, and do what you enjoy while making money.

There are so many options for getting started, whether it’s finding investors, applying for an SBA loan, or simply plying your trade online.

Whatever your path, we hope it’s one filled with joy, passion, and light.

Article resources

American Psychological Associations. (2011). Stressed in America.

Key crowdfunding statistics. (2018). 

Learn how to sell on Etsy. (n.d.).

Loans. (n.d.). 

Write your business plan. (n.d.).